1-(1,2,3,4,5-Pentahydroxypent-1-yl)-1,2,3,4-tetrahydro-beta-carboline-3-carboxylate (CHEM040922)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-27 01:04:53 UTC
Update Date2016-11-09 01:22:21 UTC
Accession NumberCHEM040922
Identification
Common Name1-(1,2,3,4,5-Pentahydroxypent-1-yl)-1,2,3,4-tetrahydro-beta-carboline-3-carboxylate
ClassSmall Molecule
DescriptionThe novel carbohydrate-derived b-carboline, 1-pentahydroxypentyl-1,2,3,4-tetrahydro-b-carboline-3-carboxylic acid, was identified in fruit- and vegetable-derived products such as juices, jams, and tomato sauces. This compound occurred as two diastereoisomers, a cis isomer (the major compound) and a trans isomer, ranging from undetectable amounts to 6.5 ug/g. Grape, tomato, pineapple, and tropical juices exhibited the highest amount of this alkaloid (up to 3.8 mg/L), whereas apple, banana, and peach juices showed very low or nondetectable levels. This tetrahydro-b-carboline was also found in jams (up to 0.45 ug/g), and a relative high amount was present in tomato concentrate (6.5 ug/g) and sauce (up to 1.8 ug/g). This b-carboline occurred in fruit-derived products as a glycoconjugate from a chemical condensation of d-glucose and l-tryptophan that is highly favored at low pH values and high temperature. Production, processing treatments, and storage of fruit juices and jams can then release this b-carboline. Fruit-derived products and other foods containing this compound might be an exogenous dietary source of this glucose-derived tetrahydro-b-carboline.(PMID: 12137498).
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
1-(1,2,3,4,5-Pentahydroxypent-1-yl)-1,2,3,4-tetrahydro-b-carboline-3-carboxylateGenerator
1-(1,2,3,4,5-Pentahydroxypent-1-yl)-1,2,3,4-tetrahydro-b-carboline-3-carboxylic acidGenerator
1-(1,2,3,4,5-Pentahydroxypent-1-yl)-1,2,3,4-tetrahydro-beta-carboline-3-carboxylic acidGenerator
1-(1,2,3,4,5-Pentahydroxypent-1-yl)-1,2,3,4-tetrahydro-β-carboline-3-carboxylateGenerator
1-(1,2,3,4,5-Pentahydroxypent-1-yl)-1,2,3,4-tetrahydro-β-carboline-3-carboxylic acidGenerator
1,2,3,4-Tetrahydro-1-(1,2,3,4,5-pentahydroxypentyl)-b-carboline-3-carboxylic acidHMDB
1-C-(3-Carboxy-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indol-1-yl)pentitol, 9ciHMDB
1-(1,2,3,4,5-Pentahydroxypentyl)-1H,2H,3H,4H,9H-pyrido[3,4-b]indole-3-carboxylateHMDB
Chemical FormulaC17H21N2O7
Average Molecular Mass365.358 g/mol
Monoisotopic Mass365.135 g/mol
CAS Registry NumberNot Available
IUPAC Name1-(1,2,3,4,5-pentahydroxypentyl)-1H,2H,3H,4H,9H-pyrido[3,4-b]indole-3-carboxylic acid
Traditional Name1-(1,2,3,4,5-pentahydroxypentyl)-1H,2H,3H,4H,9H-pyrido[3,4-b]indole-3-carboxylic acid
SMILESOCC(O)C(O)C(O)C(O)C1NC(CC2=C1NC1=C2C=CC=C1)C([O-])=O
InChI IdentifierInChI=1S/C17H22N2O7/c20-6-11(21)14(22)16(24)15(23)13-12-8(5-10(19-13)17(25)26)7-3-1-2-4-9(7)18-12/h1-4,10-11,13-16,18-24H,5-6H2,(H,25,26)/p-1
InChI KeyLCHFAYIGHOVWSA-UHFFFAOYSA-M
Chemical Taxonomy
Description belongs to the class of organic compounds known as 8-prenylated xanthones. These are organic compounds containing a C5-isoprenoid group linked to a xanthone moiety at the 8-position. Xanthone is a tricyclic compound made up of two benzene rings linearly fused to each other through a pyran ring that carries a ketone group.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassBenzopyrans
Sub Class1-benzopyrans
Direct Parent8-prenylated xanthones
Alternative Parents
Substituents
  • 4-prenylated xanthone
  • 8-prenylated xanthone
  • Chromone
  • 1-hydroxy-2-unsubstituted benzenoid
  • Pyranone
  • Pyran
  • Benzenoid
  • Heteroaromatic compound
  • Vinylogous acid
  • Polyol
  • Oxacycle
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organooxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility18.1 g/LALOGPS
logP-1.6ALOGPS
logP-4.1ChemAxon
logS-1.3ALOGPS
pKa (Strongest Acidic)3.04ChemAxon
pKa (Strongest Basic)6.55ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count8ChemAxon
Polar Surface Area166.27 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity89.22 m³·mol⁻¹ChemAxon
Polarizability37.56 ųChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-07bb-9086000000-f9817373dcbb48a00eadSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (4 TMS) - 70eV, Positivesplash10-066r-1092238000-8a73a9d7c71faf707742Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014j-2019000000-f66e1f938b58a2d0ba87Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-9453000000-e1c15a39669221325154Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014i-9820000000-4592a1a9ad5f5701322fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0q4u-7098000000-cf33a70ee23840fab676Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0abl-8191000000-35b3333d76ce8a3c796cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9030000000-f91a3596176e7837fc7fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0396000000-d827a244ffe0a2c0c6faSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00kb-0290000000-97bec0f48574a53ed071Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0fr2-0690000000-7c1bfbeb116d5b8be2c9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00kb-0019000000-9f6a5ad048923d81db75Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-015a-0039000000-ec40574589c9a65187f8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0fr7-1950000000-243db3326d0d83bf067dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00os-0095000000-434183b2caa2a5fc0e2eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-002b-0290000000-cd470a35408a3c672cb4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00kb-0790000000-268f41ef52f47148a6abSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00l2-0019000000-bcc589f4c881eb9d4a53Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-015a-0029000000-56506c109d6f5437d8feSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0un9-2790000000-3d689c092b66a1e858f9Spectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0012492
FooDB IDFDB001280
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID19993304
ChEBI ID169367
PubChem Compound ID21125948
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Herraiz T, Galisteo J: Identification and occurrence of the novel alkaloid pentahydroxypentyl-tetrahydro-beta-carboline-3-carboxylic acid as a tryptophan glycoconjugate in fruit juices and jams. J Agric Food Chem. 2002 Jul 31;50(16):4690-5.